Stock-Based Compensation | Stock-Based Compensation 2008 Stock Option Plan The Company maintained a stock plan, the 2008 Stock Option Plan, as amended and restated (the “2008 Plan”), which allowed the Company to grant incentive (“ISO”), non-statutory (“NSO”) stock options and restricted stock units (“RSU”) to its employees, directors and consultants to participate in the Company’s future performance through stock-based awards at the discretion of the board of directors. Under the 2008 Plan, options to purchase the Company’s common stock could not be granted at a price less than fair value in the case of ISOs and NSOs. Fair value was determined by the board of directors, in good faith, with input from valuation consultants. On June 22, 2016, the plan was terminated in connection with the Company’s IPO. Accordingly, no shares are available for future issuance under the 2008 Plan. The 2008 Plan continues to govern outstanding equity awards granted thereunder. The Company’s right of first refusal for outstanding equity awards granted under the 2008 Plan terminated upon completion of the IPO. Options granted include provisions for early exercisability. 2016 Stock Option Plan The Company’s 2016 Stock Option and Incentive Plan (the “2016 Plan”) became effective on June 21, 2016. The 2016 Plan provides for the grant of ISOs, NSOs, restricted stock, RSUs, stock appreciation rights, unrestricted stock awards, performance share awards, dividend equivalent rights and cash-based awards to employees, directors and consultants of the Company. A total of 11,500,000 shares of the Company’s Class A common stock were initially reserved for issuance under the 2016 Plan. These available shares automatically increase each January 1, beginning on January 1, 2017, by 5% of the number of shares of the Company’s Class A and Class B common stock outstanding on the immediately preceding December 31, or such lesser number of shares as determined by the Company’s compensation committee. On January 1, 2020 and 2019, the shares available for grant under the 2016 Plan were automatically increased by 6,920,640 and 5,004,011 shares, respectively. Under the 2016 Plan, the stock options are granted at a price per share not less than 100% of the fair market value per share of the underlying common stock on the date of grant. Under both plans, stock options generally expire 10 years from the date of grant and vest over periods determined by the board of directors. The vesting period for new-hire options and restricted stock units is generally a four year term from the date of grant, at a rate of 25% after one year, then monthly or quarterly, respectively, on a straight-line basis thereafter. In July 2017, the Company began granting restricted stock units to existing employees that vest in equal quarterly installments over a four year service period. SendGrid Equity Awards Assumed in Acquisition In connection with its acquisition of SendGrid, Inc. ("SendGrid"), the Company assumed all stock options and restricted stock units issued under SendGrid’s 2009, 2012 or 2017 Stock Incentive Plans that were outstanding on the date of acquisition. The assumed equity awards will continue to be outstanding and will be governed by the provisions of their respective plans. Additionally, the Company assumed shares of SendGrid common stock that were reserved and available for issuance under SendGrid's 2017 Equity Incentive Plan, on an as converted basis. These shares can be utilized for future equity grants under the Company’s 2016 Plan, to the extent permitted by New York Stock Exchange rules. 2016 Employee Stock Purchase Plan The Company’s Employee Stock Purchase Plan (“2016 ESPP”), as amended, initially became effective on June 21, 2016. A total of 2,400,000 shares of the Company’s Class A common stock were initially reserved for issuance under the 2016 ESPP. These available shares automatically increase each January 1, beginning on January 1, 2017, by the lesser of 1,800,000 shares of the common stock, 1% of the number of shares of the Company’s Class A and Class B common stock outstanding on the immediately preceding December 31 or such lesser number of shares as determined by the Company’s compensation committee. On January 1, 2020 and 2019, the shares available for grant under the 2016 ESPP were automatically increased by 1,384,128 and 1,000,802 shares, respectively. The 2016 ESPP allows eligible employees to purchase shares of the Company’s Class A common stock at a discount of up to 15% through payroll deductions of their eligible compensation, subject to any plan limitations. The 2016 ESPP provides for separate six On each purchase date, eligible employees purchase the Company’s stock at a price per share equal to 85% of the lesser of (i) the fair market value of the Company’s Class A common stock on the offering date or (ii) the fair market value of the Company’s Class A common stock on the purchase date. In the three months ended September 30, 2020 and 2019, no shares of Class A common stock were purchased under the 2016 ESPP, respectively, and 103,374 shares are expected to be purchased in the fourth quarter of 2020. As of September 30, 2020, total unrecognized compensation cost related to the 2016 ESPP was $1.6 million, which will be amortized over a weighted-average period of 0.1 years. Stock Options Stock option activity under the Company's 2008 Plan and 2016 Plan as well as respective Stock Incentive Plans assumed in the SendGrid acquisition was as follows: Number of Weighted- Weighted- Aggregate Outstanding options as of December 31, 2019 7,150,848 $ 28.79 6.47 $ 511,971 Granted 599,909 127.74 Exercised (3,110,685) 20.15 Forfeited and canceled (248,152) 71.27 Outstanding options as of September 30, 2020 4,391,920 $ 46.02 6.61 $ 883,089 Options vested and exercisable as of September 30, 2020 2,678,454 $ 19.05 5.54 $ 610,799 Three Months Ended Nine Months Ended 2020 2019 2020 2019 (In thousands, except per share amounts) Aggregate intrinsic value of stock options exercised (1) $ 89,808 $ 67,952 $ 496,198 $ 355,776 Total estimated grant date fair value of options vested $ 12,090 $ 20,959 $ 53,110 $ 62,657 Weighted-average grant date fair value per share of options granted $ — $ — $ 64.06 $ 58.16 ____________________ (1) Aggregate intrinsic value represents the difference between the fair value of the Company’s Class A common stock as reported on the New York Stock Exchange and the exercise price of outstanding “in-the-money” options. On February 28, 2017, the Company granted a total of 555,000 shares of performance-based stock options in three distinct awards to an employee with grant date fair values of $13.48, $10.26 and $8.41 per share for a total grant value of $5.9 million. The first half of each award vests upon satisfaction of a performance condition and the remainder vests thereafter in equal monthly installments over a two Number of Weighted- Weighted- Aggregate Outstanding options as of December 31, 2019 555,000 $ 31.72 4.16 $ 36,941 Granted — — Exercised — — Forfeited and canceled — — Outstanding options as of September 30, 2020 555,000 $ 31.72 3.41 $ 119,530 Options vested and exercisable as of September 30, 2020 508,749 $ 31.72 3.41 $ 109,569 As of September 30, 2020, total unrecognized compensation cost related to nonvested stock options was $75.0 million, which will be amortized on a ratable basis over a weighted-average period of 2.2 years. Restricted Stock Units Number of Weighted- Aggregate Nonvested RSUs as of December 31, 2019 8,490,517 $ 74.21 $ 830,167 Granted 2,826,569 176.19 Vested (2,621,821) 70.95 Forfeited and canceled (669,076) 88.32 Nonvested RSUs as of September 30, 2020 8,026,189 $ 111.58 $ 1,979,215 As of September 30, 2020, total unrecognized compensation cost related to nonvested RSUs was $818.6 million, which will be amortized over a weighted-average period of 2.6 years. Valuation Assumptions No stock options were granted in the three months ended September 30, 2020 and 2019. The fair value of employee stock options was estimated on the date of grant using the following assumptions in the Black-Scholes option pricing model: Nine Months Ended Employee Stock Options: 2020 2019 Fair value of common stock $108.4 - $191.9 $111.3 - $130.7 Expected term (in years) 6.08 0.33 - 6.08 Expected volatility 51.9% - 56.0% 48.3% - 66.5% Risk-free interest rate 0.4% - 1.4% 2.4% - 2.5% Dividend rate —% —% Nine Months Ended Employee Stock Purchase Plan: 2020 2019 Expected term (in years) 0.50 0.50 Expected volatility 72.1% 50.3% Risk-free interest rate 0.2% 2.4% Dividend rate —% —% The following assumptions were used in the Monte Carlo simulation model to estimate the grant date fair value and the derived service period of the performance options: Asset volatility 40% Equity volatility 45% Discount rate 14% Stock price at grant date $31.7 Stock-Based Compensation Expense The Company recorded the total stock-based compensation expense as follows: Three Months Ended Nine Months Ended 2020 2019 2020 2019 (In thousands) Cost of revenue $ 2,237 $ 1,674 $ 6,217 $ 5,106 Research and development 46,294 34,348 119,344 93,388 Sales and marketing 26,573 16,143 69,602 42,456 General and administrative 14,306 16,103 42,659 56,382 Total $ 89,410 $ 68,268 $ 237,822 $ 197,332 |